Famous and wealthy funnyman George Simmons doesn't give much thought to how he treats people until a doctor delivers stunning health news, forcing George to reevaluate his priorities with a little help from aspiring stand-up comic Ira.

Andy Stitzer has a pleasant life with a nice apartment and a job stamping invoices at an electronics store. But at age 40, there's one thing Andy hasn't done, and it's really bothering his sex-obsessed male co-workers: Andy is still a virgin. Determined to help Andy get laid, the guys make it their mission to de-virginize him. But it all seems hopeless until Andy meets small business owner Trish, a single mom.

When Christy Murphy comes home past midnight with her boyfriend, Jerry, her parents send her to the Academy of the Blessed Virgin, a Catholic school run by kind but very strict nuns.